Back to EveryPatent.com
United States Patent | 5,296,588 |
Au ,   et al. | March 22, 1994 |
A process of preparing aldonamides and N-substituted aldonamides which includes the steps of recovering a by-product of the process (an ammonium salt of an aldonic acid) and converting it into at least one starting material. Aldonolactone is reacted with a primary or secondary amine and the resulting solution containing the by-product of the reaction is treated with a solid base to obtain a solid aldonate salt and a second solution containing the starting amine and some aldonamide. The second solution may be recycled as part of the starting material mixture. Alternatively, the amine and the aldonamide may be recovered from the second solution, and the amine alone may be recycled. The solid salt of aldonic acid may be converted into aldonic acid, which in turn may be converted into aldonolactone. The obtained aldono-1,5-lactone may also be utilized as a starting ingredient in the synthesis according to the present invention.
Inventors: | Au; Van (Peekskill, NY); Harirchian; Bijan (South Orange, NJ) |
Assignee: | Lever Brothers Company, Division of Conopco, Inc. (New York, NY) |
Appl. No.: | 958402 |
Filed: | October 8, 1992 |
Current U.S. Class: | 536/1.11; 536/4.1; 536/22.1; 536/124 |
Intern'l Class: | C07G 003/00; C07H 015/04; C07C 235/06 |
Field of Search: | 536/1.11,22,124,4.1,22.1 |
2662073 | Dec., 1953 | Mehltretter et al. | 536/53. |
2746916 | May., 1956 | Magariello | 536/53. |
2752334 | Jun., 1956 | Walton | 536/53. |
4774231 | Sep., 1988 | Petitou et al. | 514/53. |
Foreign Patent Documents | |||
2227008 | Nov., 1974 | FR. |
Grant et al, eds. Grant & Hackh's Chemical Dictionary, McGraw-Hill Book Company, New York, 1987, p. 21. European Search Report in European Patent Application 92204033.2. Derwent Abstract of FR 2.227.008. Taravel, Francois R. "Amphiphilic properties of synthetic glycolipids based on amide linkages, 4". Makromol. Chem. vol. 191 (1990), pp. 3097-3106. Patent Abstracts of Japan, vol. 015163, JP 3034946. Ullmann's Encyclopedia of Industrial Chemistry. vol. A14: Immobilized Biocatalysts to Isoprene, (1989), pp. 448-449. Williams, Taffy J., et al. "A New Class of Model Glycolipids: Synthesis, Characterization, and Interaction with Lectins." Archives of Biochemistry and biophysics, vol. 195, No. 1, (Jun. 1979), pp. 145-151. Kobayashi, Kazukiyo, et al. "Synthesis and Functions of Polystyrene Derivatives Having Pendant Oligosaccharides." Polymer Journal, vol. 17, No. 4, (1985), pp. 567-575. Ziegast, Gerd et al., "Coupling of mono- and oligosaccharides to .alpha.-w-diamino substituted poly(oxyethylene) and multifunctional amines by amide linkage." Makromol. Chem., Rapid Commun. vol. 5, (1984), pp. 373, 379. |